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JUN WATANABE, HIROSHI OKABE, TERUHISA ICHIHASHI, KENJI MIZOJIRI, HIDEO ...
1977 Volume 25 Issue 9 Pages
2147-2155
Published: September 25, 1977
Released on J-STAGE: March 31, 2008
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Gastric emptying rates of quinine and phenol red were investigated after oral administration of the syrup or the simple solution to mice, rats, and rabbits. These drugs in the stomach were transferred to the small intestine at a relatively fast rate in the early stage and then gradually evacuated according to first-order kinetics. In mice and rats, 24-hr fasting increased the gastric emptying rate for the simple solution of quinine. In rats, an increased volume of the simple solution gave a larger gastric emptying rate constant. Generally, smaller animals in this work had larger gastric emptying rate constants. Drugs given orally as the syrup showed slower gastric emptying rates than those given as the simple solution in almost all animals examined. The gastric emptying rate of quinine was faster than that of phenol red in 24-hr fasting rabbits. The simulated calculation for slow gastric emptying indicated that the drug level in the body is mainly controlled by the gastric emptying rate and scarcely affected by intestinal absorption rate constant, k
2, in the region where k
2 is more than 2 (hr
-1).
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AKIRA MIZUTANI, IKUKATSU SUZUKI, YOSHIHIRO MATSUSHITA, KAZUMI HAYAKAWA
1977 Volume 25 Issue 9 Pages
2156-2162
Published: September 25, 1977
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Previously we reported on the lymphocyte-stimulating activity of the hypocalcemic substances (TP
1, TP
2) which were isolated from the bovine thymic extracts, and on their possibility of promoting immune competence (A. Mizutani, et al., Ann. N. Y. Acad. Sci., 249, 220 (1975)). To acquire the direct evidence for promoting immune competence, both substances and several fractions, which were obtained from the thymic extracts in the course of purification, were examined for the increase in antibody-producing cells (PFC activity) in mice by the Jerne method with a minor change. Roughly, it was recognized that there was a tendency for the promotion of PFC activity of the fractions to be dependent on that of their hypocalcemic activity accompanied by lymphocyte-stimulating activity. In the administration of both TP
1 and TP
2, in a dose of 1 μg/mouse, to neonatal mice, significant PFC activity was found. Thus it gives a clearer understanding of the action of promoting immune competence taking the lymphocyte-stimulating action into account.
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TSUYOSHI MATSUMOTO, MASAHIRO WATANABE, TETSUO HAMANO, SHUICHI HANADA, ...
1977 Volume 25 Issue 9 Pages
2163-2171
Published: September 25, 1977
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Survival prolongation was studied in rats which were hemodiluted to a hematocrit value of as low as 7, 4, or 1% by stepwise exchange transfusion, alternating bleeding through the artery and infusing a perfluorochemical (FC) emulsion into the vein, with the combined use of oncotic agents taken into consideration to maintain the circulating plasma volume, and the following results were found : (1) Plasma expander (PE) was indispensable to the use of FC emulsion for the survival of exchange-transfused rats. As an oncotic agent to be combined with FC emulsion, homologous plasma and 6% hydroxyethyl-starch (HES) solution were better than dextran in rats. (2) At the exchange transfusion with FC emulsion+PE, totaling 1.2 times the volume of blood eliminated, survival effect was better at a ratio of FC emulsion to PE of 1 : 3 than 3 : 1. (3) Supplementary infusions of Fluosol-DA (an improved FC emulsion made isooncotic with 2.7% HES) carried out after the exchange transfusion at intervals of 24 hr were effective in prolongation of survival.
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AKIRA AKAHORI, KIYOMI KAGAWA, MASATOSHI TOGAMI, TORU IWAO
1977 Volume 25 Issue 9 Pages
2172-2180
Published: September 25, 1977
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To examine the seasonal changes of the sapogenins contained in Dioscorea tokoro MAKINO, third-year plants were cultivated on an experimental farm. Rhizome weight started to increase at the end of August, when rapid shoot growth was arrested. Rhizome enlargement was not observed in female plants. The concentrations and quantities of the sapogenins differed with the morphological part of the plant and the month of harvest. Yonogenin quantities in leaves and flowers continued to increase until the end of summer, after which its concentration was maintained in the leaves but decreased rapidly in the flowers. Most of the yonogenin in the aerial parts was degraded or transformed into other substances during September and November. Tokorogenin was present at much lower concentrations in all parts and at all times. Diosgenin was generally found in the rhizome as sugar-bound saponins, and at markedly high levels during August and October. However, four of the 84 plants used contained large quantities of diosgenin in the leaves and flowers.
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KIYOMI KIKUGAWA
1977 Volume 25 Issue 9 Pages
2181-2188
Published: September 25, 1977
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Reaction of adenosine with sulfuryl chloride gave two compounds, 5'-chloro-5'-deoxyadenosine 2', 3'-cyclic sulfate (I) and N
3, 3'-cycloadenosine derivative (II). I was converted into 2'-sulfate (III) and 3'-sulfate (IV) by treatment with aqueous alkali and into N
4, 3'-cyclo-4-aminoimidazole 5-carboxamidine nucleoside (V) by treatment in aqueous ethanol at an elevated temperature. 5'-Chloro-5'-deoxyadenosine (VI) derived from adenosine by reaction with thionyl chloride was readily converted into N
3, 5'-cycloadenosine chloride (VIII). VIII was transformed into N
4, 5'-cyclo-4-aminoimidazole 5-carboxamidine nucleoside (XII) via the unidentified characteristic compound (X) by reaction with diluted alkali. Characteristic changes of ultraviolet spectra of VIII were described.
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MASAYOSHI YAMAGUCHI, TAKEO YAMAMOTO
1977 Volume 25 Issue 9 Pages
2189-2194
Published: September 25, 1977
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Calcitonin (CT) administered subcutaneously to intact and thyroparathyroidectomized rats caused a significant decrease in the serum calcium, while the serum glucose concentration increased. The maximal response was obtained with 80 MRC mU/100 g body weight. The lowest dose of CT which produces a detectable effect was approximately 20 MRC mU. Glucagon (5 μg/100 g) caused a rapid elevation in the serum glucose, reaching a maximum level within 15 min, whereas CT caused a more gradual increase in the serum glucose, reaching a maximum after 60 min. Administration of CT to fasted rats caused a significant increase in the serum glucose. Liver glycogen levels were relatively decreased by CT administration. Administration of CT produced the accumulation of calcium in liver cells and significantly elevated glucose-6-phosphatase and phosphorylase activities in liver homogenate. These results suggest that a rise in the serum glucose concentration produced by CT may involve the production of glucose in the liver.
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USHIHO MATSUMOTO, KENJI SHIMADA, MITSUO IKEDA, IKUTO HAYAKAWA, YUZO NA ...
1977 Volume 25 Issue 9 Pages
2195-2202
Published: September 25, 1977
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A method of tritiation and application to chemical determination of insulin are presented. Tritium labeling of insulin is performed by a catalytic exchange method with tritiated phosphoric acid-boron trifluoride complex, which is prepared by the use of tritiated water (100 mCi/ml). Bovine crystalline insulin was tritiated with this reagent for 12 hr at room temperature, and the product was confirmed to be identical with unlabeled intact insulin by several chromatographic techniques. Specific radioactivity of
3H-insulin was 6.2-6.5 mCi/mmol. The most effective coupling condition for
3H-insulin with phenyl isothiocyanate [
35S] was at 40°and pH 9.0 in N, N-dimethylallylamine-TFA buffer for 4 hr, which gave a single radioactive peak of
35S-bis (phenylthiocarbamyl)-
3H-insulin on radio-paper scannogram. On the double isotope derivative dilution analysis, the radioactive portion was eluted from the paper and the radioactivities of
3H and
35S were measured by a liquid scintillation spectrometer. The loss of insulin through the analytical procedures can be corrected by the use of
3H-insulin added as an internal indicator. The recovery of authentic insulin was 101.5±1.4 to 104.1±3.4%. When
3H-insulin of the present specific radioactivity is used, the determination limit of the method for insulin is 100 μg (0.017 μmol). This isotope derivative method will be available for corrections of the overestimated values obtained by the routine radioimmunoassay as total immunoreactive insulin levels.
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YUTAKA SEKINE, MIE MIYAMOTO, MASAHISA HASHIMOTO, KIYOSHI NAKAMURA
1977 Volume 25 Issue 9 Pages
2203-2210
Published: September 25, 1977
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The pharmacokinetic studies of piromidic acid (PA, 5, 8-dihydro-8-ethyl-5-oxo-2-pyrrolidinopyrido [2, 3-d] pyrimidine-6-carboxylic acid=2-pyrrolidino-PPA) were performed in human subjects after oral administration. A compartment model involved thirteen parameters was adopted, in which PA compartment was connected to each compartment in branched metabolic pathway. Each parameter was determined by mathematical method, and a trial and error procedure using the experimental data on blood levels and urinary excretion in man receiving oral PA. Calculated urinary excretion of PA or its metabolites was found to be reasonable. Combined amounts calculated for biological active materials, PA, M-II (2-(2-hydroxypyrrolidino)-PPA) and M-V (2-(3-hydroxypyrrolidino)-PPA) were found to be in good agreement with those by bioassay, demonstrating that this pharmacokinetic model is valid to lead to better understanding of chemotherapeutic effect of PA.
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YUTAKA ASAHI, TOSHIKO YOSHIDA
1977 Volume 25 Issue 9 Pages
2211-2216
Published: September 25, 1977
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Cartap hydrochloride, 1, 3-bis (carbamoylthio)-2-N, N-dimethylaminopropane hydrochloride (I), an insecticide, hydrolyzes to 1, 3-dimercapto-2-N, N-dimethylaminopropane (II) which are oxidized to nereistoxin, 4-N, N-dimethylamino-1, 2-dithiolane (III). The hydrolysis was a base-catalyzed pseudo-first-order reaction, of which the rate constants were measured by a pH stat method and polarography in pH 4-12 at 0°and 25°. For example, the half-life (t
1/2) at pH 7 was 10 min at 25°. III was so stable that no degradation was observed after 24 hr at 100°in pH 1-4 and that t
1/2 at pH 7 was to be 2.4 years at 25°. However the disulfide (III) hydrolyzes to 2-N, N-dimethylamino-3-mercaptopropanesulfenic acid (IV) at pOH 1.1 with t
1/2 2.2 hr at 100°. The isomer of I, 2, 3-bis (carbamoylthio)-N, N-dimethylpropylamine hydrochloride (VII), hydrolyzes 10 times as rapid as I.
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SHIGEO FUKUCHI, KAZUNORI KATAYAMA, MASAWO KAKEMI, MICHIHIRO UEDA, TAMO ...
1977 Volume 25 Issue 9 Pages
2217-2224
Published: September 25, 1977
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The purpose of this study was to represent quantitatively the relationship between the time course of pharmacological response and drug disposition data after intravenous administration of furosemide in rabbits. After administration of furosemide, urine flow rate, urinary excretion rate of Na
+ and K
+ were measured as well as excretion rate of intact drug and drug plasma level. From the data observed, a simplified simulation model was constructed and theoretical values were calculated by the model. Calculated values showed reasonable coincidence with the observed values. The urinary excretion rate of furosemide which was used in place of the plasma level, for the practical purposes, was able to correlate quantitatively with diuretic response ; urine flow rate and electrolyte excretion rate.
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MITSUO UCHIDA, TAKEO HIGASHINO, EISAKU HAYASHI
1977 Volume 25 Issue 9 Pages
2225-2230
Published: September 25, 1977
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Mass spectra (MS) of 3-alkyl-4-cinnolinecarbonitrile (I) were examined. In MS of I, (M-·H)
+ species are encountered only to a minor extent in the lower one in contrast with (M-·N
2H)
+ species. In particular it is worth noting that (M-·H)
+ species are not found in MS of 3-methy1-(Ib) and 3-ethyl-4-cinnolinecarbonitrile (Ic). When the alkyl substituent at the 3-position of I such as methyl (Ib), ethyl (Ic), and propyl (Id), is not so bulky, the important fragmentation arises from the initial expulsion of ·N
2H radical from M
+. In turn, when the alkyl substituent is bulkier than that of isopropyl, the importance of this process is not recognized as seen in MS of 3-isopropyl-(Ie) and 3-butyl-4-cinnolinecarbonitrile (If). Those facts mentioned above mean that the ring cleavage of I by the initial expulsion of ·N
2H radical is dependent on the relative size of the alkyl substituent at the 3-position.
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TETSUO NOGUCHI, KADZUYA TANIGUCHI, TOSHIKO YOSHIFUJI, SHOZO MURANISHI, ...
1977 Volume 25 Issue 9 Pages
2231-2238
Published: September 25, 1977
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Lymphatic and plasma levels of griseofulvin were determined in the rat after intraluminal administration as an oil-in-water emulsion dosage form. Compared with oral administration, peak plasma levels are attained in a very short time. This finding supports the proposed mechanism that the bioavailability of orally administered griseofulvin was improved by inhibition of gastric motility. Although peak lymphatic level is reached more slowly than the peak plasma level, griseofulvin peak concentration is almost as high, suggesting that the lymphatic appearance of griseofulvin is due to its distribution in the body water, of which lymph is a part. The possible factors determining the extent of lymphatic absorption of lipid-soluble compounds have been discussed with the special reference to their dissolution characteristics in vitro. Two groups (lymph/plasma>1 and lymph/plasma⪈1) related to the ratio of dissolution rates in an oil-in-water emulsion and in 6% BSA solution are distinguished. It is suggested that one of the major factors determining the extent of lymphatic absorption is the affinity with carriers in the portal route rather than that with lymphatic ones.
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ATSUSHI WATANABE, YUMIKO TANAKA, YOKO TANAKA
1977 Volume 25 Issue 9 Pages
2239-2243
Published: September 25, 1977
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The microscopic study of crystalline substances using a polarizing microscope and the immersion media was shown to have an advantage of simple and rapid identification of drugs, especially in polymorphs or solvates. Examples of the application of this technique were given for four crystal forms of thiamine hydrochloride, two forms of each bromvalerylurea and ampicillin. The accuracy and reproducibility of the measured refractive indices are discussed with its relation to crystal habit.
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SHIGERU KOBAYASHI, HIDEKI ISHIKAWA, MASARU KIHARA, TETSURO SHINGU, TOS ...
1977 Volume 25 Issue 9 Pages
2244-2248
Published: September 25, 1977
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The bulbs of Zephyranthes carinata HERB. (Amaryllidaceae) were found to contain pretazettine (I) and a new phenolic base, carinatine (II), as well as lycorine (III), galanthine (IV), and haemanthamine (V). Carinatine (II), C
17H
21NO
4■, was established to be O-demethylgalanthine.
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EIICHI YOSHII, TAKIKO ORIBE, TORU KOIZUMI, ICHIHIRO HAYASHI, KUMIKO TU ...
1977 Volume 25 Issue 9 Pages
2249-2256
Published: September 25, 1977
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An efficient synthetic method of bufa-20, 22-dienolides from 20-ketopregnanes has been developed. The method involves the following reaction sequence : (1) 21-methoxy-methylenation, (2) 2-methoxydihydropyrane formation by reaction with excess dimethylsulfonium methylid, (3) transformation to buf-20 (22)-enolide structure, (4) dehydrogenation to bufa-20, 22-dienolide. Application of this attractive device to readily available 3β-acetoxy-5β-pregn-14-en-20-one established a new route to resibufogenin and bufalin.
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KAZUAKI KUKINO, TAKASHI DEGUCHI
1977 Volume 25 Issue 9 Pages
2257-2262
Published: September 25, 1977
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The effects of sodium dipropylacetate (DPA) on the metabolisms of γ-aminobutyric acid (GABA) and biogenic amines in the rat brain have been investigated. The results obtained are as follows, which are suggestive of the mechanism of anticonvulsant activity of DPA. 1) The level of GABA in the brain was elevated after oral administration (400 mg/kg). At the peak time (0.5 hr), about 45% increase was observed and the elevation of GABA content wsa maintained for 4 hr after administration. 2) In the brain slices, DPA elevated GABA content and suppressed the oxygen consumption at 6 mM. 3) DPA had weak inhibitory effects on GABA metabolizing enzymes in brain homogenate. 4) The concentrations of 5-hydroxyindoleacetic acid and tryptophan in the brain were elevated after oral administration of DPA (400 mg/kg). These effects might be caused by the increase of free tryptophan in the serum followed by accelerated incorporation of tryptophan into the brain and the elevated turnover rate of 5-hydroxytryptamine in the brain. 5) DPA elevated the content of dopamine, but the level of norepinephrine was not affected. The changes of thess biogenic substances were coincident with the appearance of the anticanvulsant activity of DPA.
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YUKIO SUGIURA, NAKAO KOJIMA, HISASHI TANAKA
1977 Volume 25 Issue 9 Pages
2263-2266
Published: September 25, 1977
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In (III) and Ga (III) binding by new ligands, 2, 3-dimercaptopropionylglycine (DMPG) and 2-mercaptopropionyl-L-cysteine (MPC), which involve two adjacent and separated sulfhydryl groups, has been investigated with proton nuclear magnetic resonance spectra. The methylene protons of the 2 : 1 DMPG-In (or Ga) complex were observed as two signals at 3.28 and 3.02 (or 3.33 and 2.98) ppm, indicating a fused-chelate ring formation. On the other hand, MPC formed a polymer In species in addition to the 2 : 1 MPC-In (or Ga) complex which has a rigid configuration similar to the 2 : 1 DMPG-In (or Ga) complex. The coupling constants between the methylene and methine protons and the structure for these In and Ga complexes have been discussed.
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HIROSHI SAKAGUCHI, HIROHI ANZAI, KIMIO FURUHATA, HARUO OGURA, YOICHI I ...
1977 Volume 25 Issue 9 Pages
2267-2272
Published: September 25, 1977
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The crystal structure of Zn (II) complex of 2-hydrazino-4-hydroxy-6-methylpyrimidine (LH), has been determined from three-dimensional X-ray diffractometer data by heavy atom Fourier methods. Crystals of [Zn(C
5H
8N
4O)
2 (H
2O)
2] Cl
2·2H
2O are triclinic with unit cell dimensions a=8.912 (3), b=9.298 (2), c=6.821 (5) A, α=93.11 (5)°, β=102.14 (4)°, γ=114.33 (2)°, space group P^^1, and Z=1. Block-diagonal least-squares refinement using 1537 independent reflexions yielded the R value of 0.050. The zinc (II) ion completes an octahedral coordination with two ring nitrogen and two amino nitrogen atoms of the two neighbouring ligand molecules and two water molecules. The chloride ions are not bonded to zinc (II) ion but to N (1)-H of the pyrimidine base.
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TAKASHI HARAYAMA, HIDETSURA CHO, YASUO INUBUSHI
1977 Volume 25 Issue 9 Pages
2273-2282
Published: September 25, 1977
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The detailed studies on the stereochemistry of the Diels-Alder adducts of 2, 5-dialkyl-cyclohex-2-en-1-one with butadiene in the presence of Lewis acid were made. The experimental results indicated that addition of butadiene to the dienophile took place stereoselectively opposite to the 5-alkyl side. This fact is in conflicting with the former results [see ref.4)] that addition of butadiene in the Diels-Alder reaction of carvone with butadiene occurred predominantly from the same side as that of the 5-isopropenyl group. The reported reaction, therefore, was re-investigated. It was concluded from the results of experiments that addition of butadiene took place predominantly opposite to the 5-isopropenyl side in a similar manner as our deduction. Consequently, the reported stereostructures [see ref.4)] should be revised in such a way that the structure (3b) for the major product is replaced by the formula (3a) and the structure (3a) for the minor product by the formula (3b). The reaction condition was also examined and the yield of the major product (3a) was much improved in the presence of 0.11 eq AlCl
3 to the dienophile at room temperature under vigorous stirring.
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HIDEMI ISHII, TETSUYA SUGA, SHINKICHI NIINOBE, YOSHIHIKO INATSU
1977 Volume 25 Issue 9 Pages
2283-2286
Published: September 25, 1977
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The effect of 3-amino-1, 2, 4-triazole (AT) on the formation of liver triglyceride (TG) was studied by using liver slices. In the liver of rat received AT (1 g/kg, i.p.), the incorporation of
14C-acetate into TG decreased about 45 per cent when compared with that of the control, though the incorporation of
14C-palmitate into TG did not differ from that of the control. In addition, the incorporation of
14C-acetate into total fatty acid decreased about 30 per cent in the liver of the received with AT. In in vitro experiment, the incorporation of
14C-acetate into TG was inhibited about 40 per cent in the presence of 50 mM AT in incubation mixture and the inhibition was dependent to the concentration of AT. One of the causes of decrease of liver TG level induced by AT may be due to the inhibition of fatty acid synthesis in the liver.
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TOMEI OGURI, TAKAYUKI SHIOIRI, SHUNICHI YAMADA
1977 Volume 25 Issue 9 Pages
2287-2291
Published: September 25, 1977
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The Schiff base (I) from glycine tert-butyl ester and benzaldehyde was treated with lithium diisopropylamide to give the corresponding α-carbanion. Alkylation of the α-carbanion with benzyl or butyl halide followed by removal of benzylidene group yielded phenylalanine or norleucine tert-butyl ester (IIa or IIb), accompanied by dialkylated product (IIIa or IIIb). The Schiff base (IV) from alanine tert-butyl ester and (-)-men-thone (VI) was also treated as above to furnish α-methylphenylalanine or α-methyl-β-(3, 4-dimethoxyphenyl) alanine tert-butyl ester (Va or Vb) in 21 or 24% asymmetric yield.
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KENTARO HIRAI, HIROHIKO SUGIMOTO
1977 Volume 25 Issue 9 Pages
2292-2299
Published: September 25, 1977
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A novel method of synthesizing 2-disubstituted-amino-4-arylthiazol-5-ylalkanoic acids (3) was studied. Dehydration of S-(α-benzoyl-β-ethoxycarbonyl) ethyl 1-piperidinethiocarbonate (5a) in the presence of aqueous perchloric acid-acetic anhydride yielded 4-ethoxycarbonyl-methyl-5-phenyl-2-piperidino-1, 3-oxathiolium perchlorate (1a). Nucleophilic reaction of ammonia with 1a afforded 5-ethoxycarbonylmethyl-4-phenyl-2-piperidinothiazole (2a). Acid-catalyzed hydrolysis of 2a gave 3a as a hydrochloride. The acids (3) were also synthesized by the classical Hantzsch method. These alkanoic acids were evaluated as antiinflammatory agents on carrageenin-induced abscess in rat.
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GENICHIRO NONAKA, MASAFUMI MINAMI, ITSUO NISHIOKA
1977 Volume 25 Issue 9 Pages
2300-2305
Published: September 25, 1977
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A new stilbene glycoside (I), mp 258°, [α] D-86.0°, C
27H
26O
12·1/2H
2O, together with 3, 5, 4'-trihydroxystilbene 4'-O-β-D-glucopyranoside (II) and d-catechin (III), was isolated from the Japanese rhubarb, "Shinshu Daio", and the structure of I was established to be 3, 5, 4'-trihydroxystilbene 4'-O-β-D-(6''-O-galloyl)-glucopyranoside on the bases of chemical and spectral evidence. The occurrences of the stilbene glycosides (I, II) and III in commercial Chinese rhubarbs were examined by thin-layer chromatography, which revealed that almost all kinds of rhubarbs contained II and III while I appeared in the limited ones.
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YUKIHIRO SHOYAMA, HITOTOSHI HIRANO, HIROKO MAKINO, NAOHIRO UMEKITA, IT ...
1977 Volume 25 Issue 9 Pages
2306-2311
Published: September 25, 1977
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Four new cannabinoid acids, tetrahydrocannabivarinic acid, cannabidivarinic acid, cannabichromevarinic acid and cannabigerovarinic acid were isolated from Thai Cannabis, 'Meao variant'and these structures were elucidated on the basis of chemical and spectral data. This is the first example of the isolation of propyl cannabinoid acid from Cannabis.
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NOBUYOSHI KANENIWA, AKIKO IKEKAWA
1977 Volume 25 Issue 9 Pages
2312-2329
Published: September 25, 1977
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Variation in the molecular weight distribution of polyvinylpyrrolidone (PVP) by ball-milling in various kinds of atmosphere in the absence and in the presence of various kinds of organic and inorganic additives was investigated. A line broken at several points was obtained by the logarithmic plot of -log R versus the molecular weight of PVP, M
u, and equation (1) was applied in the limited range of M
u, respectively, where R was the ratio of the weight of the polymers of molecular weight above M
u to the total weight of the polymers, and k and n were parameters dependent on the experimental conditions and so on. R=exp (-kM
nu) (1) The existence of the critical molecular weight, M
c, was observed, at the region of M
u below which n was larger than 1.0 and formation of the polymers of M
u below M
c was considered to become more difficult with a decrease of M
u. The value of M
c was below 4×10
5 and varied remarkably by the kind of the additive and by the ball-milling atmosphere. Theoretical consideration was made on the molecular weight distribution of the polymers formed by chain scission of polymers by application of the mechanical stress, by assuming that chain scission was produced by activation of the bonds between atoms of the main chain by the mechanical stress and that these activated bonds were distributed at random and obeyed to Poisson's distribution law. It was suggested from the consideration mentioned above and from the investigation of the value of n in equation (1) and of the variation of R with the ball-milling time that, in many cases, random chain scission was most probable and that the density of the activated bonds over a polymer of low molecular weight was approximately equal to or higher than the density over a polymer of high molecular weight.
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HIROMU SAKURAI, MASAHIRO KITO
1977 Volume 25 Issue 9 Pages
2330-2335
Published: September 25, 1977
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The aromatic methyl group migration and hydroxylation of p-toluidine by several Fe (II)-thiol compound and hemin-thiol compound systems were investigated as a model of cytochrome P-450 of liver microsomes. In these systems, 4-hydroxy-m-toluidine, 3-hydroxy-p-toluidine and 2-hydroxy-p-toluidine were formed as the main products of the reaction. The yield of methyl group migration and hydroxylation were dependent on the type of thiol compounds, chemical form of iron (Fe (II) or hemin), pH of the reaction mixture, reaction periods as well as on the concentration of the substrates or the thiol compounds. These results on the methyl group migration of p-toluidine suggest that the Fe (II)-thiol and hemin-thiol systems can be regarded as a good chemical model for the study of the function and structure of cytochrome P-450.
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TOZO FUJII, KIYOSHI YOSHIDA, MASASHI OHBA, SHIGEYUKI YOSHIFUJI
1977 Volume 25 Issue 9 Pages
2336-2342
Published: September 25, 1977
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The mercuric acetate-(ethylenedinitrilo) tetraacetic acid oxidation of 1-(3, 4-dimethoxyphenyl)-2-(3-substituted piperidino) ethanols (7c-f), which carry the n-butyl, isopropyl, benzyl, and phenyl group as the 3-substituent in the piperidine ring, has been found to produce the corresponding 2- (8c-f) and 6-piperidones (12c-f) in good yields in ratios of 41 : 59, 29 : 71, 26 : 74, and 15 : 85. It is suggested that the 3-substituents exert both steric and electronic effects. The structures of the lactam alcohols (8c-f, 12c-f) have been confirmed by the chemical correlation with the known pyridones (11c-f, 15c-f) through the lactams (10c-f, 14c-f). The starting piperidinoethanols (7c-f) have been synthesized from the 3-substituted pyridines (5c-f) by quaternization with 3, 4-dimethoxyphenacyl bromide followed by catalytic and sodium borohydride reductions.
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ISAO KITAGAWA, TSUTOMU NAKANISHI, YOSHINOBU MORII, ITIRO YOSIOKA
1977 Volume 25 Issue 9 Pages
2343-2349
Published: September 25, 1977
Released on J-STAGE: March 31, 2008
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By using the soil bacterial hydrolysis method for a glycoside mixture isolated from the subterranean part of Metanarthecium luteo-viride MAXIM. (Liliaceae), a mixture of prosapogenols has been isolated. Purification of the mixture by repeated chromatography and acetylation, a prosapogenol has been isolated as its peracetate. On the basis of chemical and physicochemical evidence, the structure of the peracetate has been established as a pentaacetate of 11-α-L-arabinopyranosyloxy-2β, 3β-dihydroxy-25R-spirost-4-ene (=11-O-α-L-arabinopyranosyl-protometeogenin) (8a) and it has been shown that protometeogenin is a genuine sapogenol of meteogenin (3) which is one of nine spirostane-type sapogenols hitherto isolated from the titled plant and is characterized by having an A-ring aromatized spirostanol skeleton.
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TOHRU HINO, MAMORU ENDO, MASAKATSU TONOZUKA, YOSHIKO HASHIMOTO, MASAKO ...
1977 Volume 25 Issue 9 Pages
2350-2358
Published: September 25, 1977
Released on J-STAGE: March 31, 2008
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Bromination of 2-ethylthioindoles (6a, c) and 2-bromoindole (6e) with N-bromosuccinimide (NBS) in carbon tetrachloride gave 3-bromoindolenines (8). On the other hand, bromination of 2-ethylsulfonylindoles (6b, d) with NBS in methylene chloride gave 1-bromoindoles (7b, d) which were converted to 8 on heating. Both 1-bromoindoles and 3-bromoindolenines act as brominating agents for skatole or 3-phenylindole. Heating of 3-bromo-2-ethylthio-3-phenylindolenine (8c) in carbon tetrachloride gave the 6-bromoindole (11), while the 2-ethylsulfonyl derivative (8d) gave 5-bromoindole (13). However, 2, 3-dibromo-3-phenylindolenine (8e) in acetic acid was converted to 6-bromo-(main) (17) and 5-bromoindole (18) (minor). 3-Bromoindolenines (8a, b, d) gave the oxindoles (19) accompanied with the migration of the 2-substituent on treatment with ethanolic hydrochloric acid, while some 3-alkoxyoxindoles (21, 22, 23) were obtained on treatment with alcohol and base. On the other hand, the 1-bromoindole (7b) was converted to the indole (6b) under various conditions.
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MASAYUKI ONDA, RYOJI MATSUI, YASUMASA SUGAMA
1977 Volume 25 Issue 9 Pages
2359-2368
Published: September 25, 1977
Released on J-STAGE: March 31, 2008
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Twice annulations of 6, 7-dimethoxy-3, 4-dihydroisoquinoline hydrochloride (7) stereoselectively give the pseudoberbenone (12), the catalytic reduction of which preferentially affords the alloberbanone (15). On a series of reactions (oxidation, O-methylation, sodium borohydride reduction, ether cleavage and catalytic reduction) 12 is converted into the berbanone (25) via the berbadienone (21). Oxidations of 15 and 25 with mercuric acetate smoothly afford the 1, 11-didehydro compounds (17) and (26), respectively. Two isomeric metho salts (18) and (19) obtained from 17, and the one (31) from 21 are found to give the starting materials by demethylation under conditions of the Hofmann degradation. Stereostructures of the compounds obtained here are examined on the basis of the infrared and nuclear magnetic resonance spectra. Their formation pathways are also discussed.
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HIROSHI NAKAMURA, ZENZO TAMURA
1977 Volume 25 Issue 9 Pages
2369-2377
Published: September 25, 1977
Released on J-STAGE: March 31, 2008
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Colorimetric and fluorometric methods for the determination of Bunte salts have been developed. Bunte salts are reduced with dithiothreitol (DTT) to monothiols and bisulfite. The latter is determined colorimetrically with a basic fuchsine reagent in the presence of mercuric chloride or fluorometrically with N-(p-dimethylaminophenyl)-1, 4-naphthoquinoneimine in the presence of a mixture of p-chloromercuribenzoic acid and sodium arsenite. The sulfhydryl reagents and arsenite mask the thiols by forming mercaptides and a DTT-arsenite complex, respectively. The colorimetric and the fluorometric methods can determine Bunte salts in a range of 5×10
-9 to 1×10
-7 mol and 2×10
-8 to 1.5×10
-7 mol, respectively.
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YOSHIHIRO NISHIKAWA, KIMIHIRO YOSHIMOTO, TAKAHIKO MANABE, TETSURO IKEK ...
1977 Volume 25 Issue 9 Pages
2378-2384
Published: September 25, 1977
Released on J-STAGE: March 31, 2008
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A series of commercially available, non-ionic surfactants produced by partial acylation of sucrose with the hydrogenated beef-tallow fatty acids, that is, the eight kinds of DK-esters containing the mono-, di-, tri-, and polyesters of stearic and palmitic acids at different ratios were tested for their antitumor effect against Ehrlich ascites carcinoma by total packed cell volume (TPCV) method. The anti-leukemia activity of these DK-esters, as well as of the sucrose-monostearate preparation (SS-C), was also examined by tissue culture method, using a mouse leukemia cell line L-5178Y. Thus, the monoester constituents contained in them proved to exert inhibiting effects against both the tumors, in spite of the negative activities of the co-existing higher esters. In addition, it has been indicated that the preparation SS-C tended to exhibit antitumor effect upon the ascites sarcoma 180 implanted in mice (TPCV method and survival method), though it showed no activity against the same tumor in solid form (so-called host-mediated bioassay).
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KIMIO FURUHATA, HARUO OGURA, YOSHINORI HARADA, YOICHI IITAKA
1977 Volume 25 Issue 9 Pages
2385-2391
Published: September 25, 1977
Released on J-STAGE: March 31, 2008
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In order to elucidate the stereochemistry of 14-membered macrolactone, an X-ray crystal structural analysis of p-bromobenzoylpikromycin (C
35H
50O
9NBr·H
2O) was carried out. The crystals are monoclinic with space group P2
1 and unit cell dimensions of a=19.027 (9) Å, b=14.876 (5) Å, c=7.148 (3) Å, β=108.97 (8)°, Z=2. The crystal structure was solved by the heavy-atom method and refined by the block-diagonal least-squares method including anisotropic thermal parameters to a final R value of 0.118. The absolute configuration of pikromycin was determined on the D-desosamine moiety to be 2R, 4R, 5S, 6S, 8R, 12S, 13R, and 10E. A new "diamond lattice"conformation model D for p-bromobenzoylpikromycin is proposed based on the result of X-ray analysis.
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USHIO SANKAWA, YUTAKA EBIZUKA, TERUTAKA MIYAZAKI, YASUO ISOMURA, HIDEA ...
1977 Volume 25 Issue 9 Pages
2392-2395
Published: September 25, 1977
Released on J-STAGE: March 31, 2008
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Shikonin, a naphthoquinone contained in the root of Lithospermum officinalis var. erythrorhizon MAX. and Macrotomia euchroma (ROYLE) PAULS (Boraginaceae), showed a high antitumor activity against the ascites cells of Sarcoma 180. Shikonin completely inhibited the tumor growth at a dose of 5-10 (mg/kg/day). At a higher dose (>15 mg/kg/day) shikonin showed'toxicity, whereas at a lower dose (1 mg/kg/day) it was inactive. Four shikonin derivatives and the chromatographic fractions of the plant extracts were also tested and they showed similar antitumor activities against S-180.
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KATSUMI NANJO, KUNIO SUZUKI, MINORU SEKIYA
1977 Volume 25 Issue 9 Pages
2396-2400
Published: September 25, 1977
Released on J-STAGE: March 31, 2008
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Formic acid reduction selective at α, β-double bond of conjugated nitriles is described. Selective reduction of carbon-carbon double bond conjugated with two cyano groups or with both cyano and other electron-withdrawing group has been demonstrated with several examples by the use of the TEAF reagent (triethylamine-formic acid azeotrope) in N, N-dimethylformamide.
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SHINZO KANO, TSUTOMU YOKOMATSU, SHIROSHI SHIBUYA
1977 Volume 25 Issue 9 Pages
2401-2409
Published: September 25, 1977
Released on J-STAGE: March 31, 2008
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The reaction of 1-(2-bromo-4, 5-dimethoxybenzyl)-2, 3, 4, 5-tetrahydro-7, 8-dimethoxy-2-methyl-1H-2-benzazepine (17) with dimsylsodium afforded 13, 14-cis-5, 6, 7, 8-tetrahydro-2, 3, 10, 11-tetramethoxy-5-methyldibenz [b, f] azecine (28) and 5, 6, 7, 8, 13, 14-hexahydro-2, 3, 10, 11-tetramethoxy-5-methyl-13-(methylsulfinyl) methyldibenz [b, f] azecine (29). Similar reaction using 1-(2-bromo-4, 5-dimethoxybenzyl)-2, 3, 4, 5-tetrahydro-7-hydroxy-8-methoxy-2-methyl-1H-2-benzazepine (18) gave the 13, 14-trans-isomer (39) accompanying with the formation of 13-(methylsulfinyl) methyl derivative (40). The reaction fo the 2, 3, 4, 5-tetrahydro-8-hydroxy-1H-2-benzazepine (19) with dimsylsodium was also examined to give the 5, 6, 7, 8-tetrahydrodibenz [b, f] azecines (42) and (43), and the 5, 6, 7, 8, 13, 14-hexa-hydro-13-(methylsulfinyl) methyl derivative (44).
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MITSURU HASHIDA, SHOZO MURANISHI, HITOSHI SEZAKI
1977 Volume 25 Issue 9 Pages
2410-2418
Published: September 25, 1977
Released on J-STAGE: March 31, 2008
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The efficiency of water in oil (W/O) and gelatin microsphere in oil (S/O) emulsion as a drug delivery system for deliverying 5-fluorouracil (5-FU) specifically into lymphatics was evaluated in the rat. Following intragastric and intramuscular injection in the forms of emulsions and aqueous solution, radioactivities of
3H-labeled 5-FU or its antibacterial activities in plasma, regional lymph nodes, thoracic lymph and the injection site were compared with those following intravenous injection. W/O and S/O emulsion predominantly increased the area under the concentrationtime curve (AUC) of 5-FU in the regional lymph nodes and cumulative amount transported into thoracic lymph. A pronounced retardation of release of 5-FU and decrease of peak plasma concentration were also obtained following injection of these emulsions. In addition, a local injection of 5-FU with emulsions was confirmed to be considerably advantageous from the viewpoint of metabolic inactivation. These results suggest the superiority of W/O and S/O emulsion in a surgical adjuvant cancer chemotherapy by satisfying many of the criteria of an ideal drug delivery system. S/O emulsion exhibited the best efficacy throughout present examinations.
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TADAO FUJITA, TAKEICHI SAKAGUCHI
1977 Volume 25 Issue 9 Pages
2419-2422
Published: September 25, 1977
Released on J-STAGE: March 31, 2008
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The synthesis of complexes of platinum and palladium with adenine is reported. The composition of these polycrystalline complexes was a 1 : 1 ratio of the ligand to the metal. The coordination sites of these compounds were investigated by means of infrared (IR) spectroscopic analysis. The mixed ligand complex, Cu (adeH
2) (oxa) Cl·3/2H
2O has been prepared. The complex was characterized by elementary and IR spectroscopic analyses. In case of Cu (adeH
2) (oxa) Cl·3/2H
2O, it was assumed that the nigrogen atom N9 of adenine coordinated to Cu
2+ and that the N1 and N7 were protonated. From IR spectra of the complexes of platinum and palladium with adenine, it was supposed that N1 and N7 were the coordination sites.
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YUUSAKU YOKOYAMA, TAKAYUKI SHIOIRI, SHUNICHI YAMADA
1977 Volume 25 Issue 9 Pages
2423-2429
Published: September 25, 1977
Released on J-STAGE: March 31, 2008
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Thiol esters were directly and conveniently prepared from carboxylic acids and thiols with diphenyl phosphorazidate (DPPA) or diethyl phosphorocyanidate (DEPC) in the presence of triethylamine in dimethylformamide solution. Both aromatic and aliphatic acids easily react with both aromatic and aliphatic thiols. The method can be efficiently applied to the thiol ester synthesis with little racemization, demonstrated by the formation of ethyl thiol ester of benzoyl-L-leucine.
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ISAO KITAGAWA, HIDEAKI YAMANAKA, TSUTOMU NAKANISHI, ITIRO YOSIOKA
1977 Volume 25 Issue 9 Pages
2430-2436
Published: September 25, 1977
Released on J-STAGE: March 31, 2008
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By using the soil bacterial hydrolysis method and by enzymatic hydrolysis, spergulagenin A (1), which was previously obtained along with two oleanene-type sapogenols (oleanolic acid (2) and methyl spergulagenate (3)) by acid hydrolysis of the total saponin mixture extracted from the root of Mollugo spergula L. (Molluginaceae), has been shown to be a genuine sapogenol. In addition, enzymatic hydrolysis using crude naringinase of the same saponin mixture has led to the isolation of a new bisnorhopanetype sapogenol named spergulatriol (4). Based on the chemical and spectral evidence, the structure of spergulatriol has been elucidated to be 4 and it has been demonstrated that spergulatriol (4) is the genuine sapogenol of isoanhydrospergulatriol (5), which is a dienic bisnorhopane-type sapogenol and is isolated as a minor sapogenol from the acid hydrolysate of total saponin mixture.
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YOSHIYUKI OHSUGI, TAKASHI MATSUNO, YOSHIO TAKAGAKI
1977 Volume 25 Issue 9 Pages
2437-2443
Published: September 25, 1977
Released on J-STAGE: March 31, 2008
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The mechanism of the inhibitory effect of the newly synthesized compounds, 2, 4-bis (2-acetoxybenzamido) benzoic acid (AB-50) and 2, 4-bis (2-hydroxybenzamido) benzoic acid (AB-23, an active form of AB-50) on IgE-like antibody-mediated passive cutaneous anaphylaxis (PCA) was studied in comparison with that of disodium cromoglycate (DSCG). AB-50 had no anti-inflammatory activity in carrageenin edema assay, nor did it inhibit dermal reactions elicited by local injection of histamine, serotonin, or bradykinin. AB-23 markedly inhibited rat mast cell degranulation (RMCD) in vitro following IgE-anti-IgE interaction and antigen-induced histamine release in the rat peritoneal cavity. It was concluded that the inhibition of IgE-mediated PCA by AB-50 was based on prevention of degranulation of and thus release of chemical mediators from mast cells without direct antagonism against chemical mediators of PCA. AB-23 also inhibited non-anaphylactic histamine release from rat peritoneal mast cells induced by Compound 48/80 or dextran. While all of these activities were also shared by DSCG, AB-23 was found to be more active than DSCG with respect to inhibition of RMCD and histamine release induced by Compound 48/80.
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SHOICHIRO TAGAMI, YOSHIMICHI HORIBE, KAYO ADACHI, DENITSU SHIHO
1977 Volume 25 Issue 9 Pages
2444-2446
Published: September 25, 1977
Released on J-STAGE: March 31, 2008
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A simple and sensitive spectrophotometric method for the determination of oxalacetic acid in the presence of aluminum ion has been developed by the measurement of the difference in absorbance ΔA of the reaction mixture as a function of time.
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TENG KE LIN
1977 Volume 25 Issue 9 Pages
2446-2448
Published: September 25, 1977
Released on J-STAGE: March 31, 2008
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A structure-activity relationship based on a quantum statistical model was pursued in this study. The results of the calculations show that the model is good in relating the maximum velocity of the different acetophenone substrates for rabbit kidney reductase to the stretching vibrational frequency of the carbonyl group.
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KAZUTAKA MOMOSE, YASUO GOMI
1977 Volume 25 Issue 9 Pages
2449-2451
Published: September 25, 1977
Released on J-STAGE: March 31, 2008
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Simple technique for isolation and continuous observation of contractile response of single smooth muscle cells from vas deferens of guinea pig was examined for further investigation of contractile mechanism of smooth muscle instead of use of whole tissue. Cells were isolated by digestion with collagenase followed by mechanical agitation. Intact cells which were not stained by trypan blue and spindle shape were capable of contraction by application of calcium in a medium containing higher concentration of potassium. For continuous observation of contracting cells, the cells were perfused continuously with incubation medium on silicon-coated slide glass at 37°and degree of contraction was determined photographically with use of phase contrast microscope. By this procedure, many isolated cells could be observed before and through contraction with the same preparation.
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TADAO SAKAI, ITSUKO HARA, MASAHIRO TSUBOUCHI
1977 Volume 25 Issue 9 Pages
2451-2455
Published: September 25, 1977
Released on J-STAGE: March 31, 2008
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A new application of monoacidic dye is reported for the determination of berberine. The method is based on solvent extraction into nitrobenzene of an ion-pair compound formed between 2, 6-dichlorophenolindophenol and berberine. Berberine is determined by measuring absorbance of the extracts over the range of (1-5)×10
-6M (0.408-2.04μg/ml) at 650 nm. The molar absorptivity was 3.8×10
4l, mol
-1, cm
-1. Continuous variations plots have a maximum at 0.5 mol fraction of DCIP, indicating a 1 : 1 DCIP-berberine ratio.
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MITSURU HASHIDA, TAKUMI KOJIMA, YOSHITERU TAKAHASHI, SHOZO MURANISHI, ...
1977 Volume 25 Issue 9 Pages
2456-2458
Published: September 25, 1977
Released on J-STAGE: March 31, 2008
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A new derivative of mitomycin C, mitomycin C-agarose bead conjugate, was synthesized by using cyanogen bromide method. Biologically active mitomycin C was released successively from the conjugate with a half-life of about 6 day in vitro, and also in vivo following subcutaneous injection of conjugate.
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MASAKATSU KANEKO, HIROYUKI TANAKA, MISAKO KIMURA, BUNJI SHIMIZU
1977 Volume 25 Issue 9 Pages
2458-2460
Published: September 25, 1977
Released on J-STAGE: March 31, 2008
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5-Fluorouracil-4-O-glucuronic acid derivatives (V, VII) were synthesized by a condensation reaction of the silver salt of 2-benzyloxy-5-fluoro-4-pyrimidone with methyl 1-bromo-1-deoxy-2, 3, 4-tri-O-acetyl-α-D-glucopyranuronate and subsequent careful removal of the protecting group.
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KAZUMI AOYAMA, NOBUTOSHI TANAKA, NORIKO SUZUKI, TAKAO MURAKAMI, YASUHI ...
1977 Volume 25 Issue 9 Pages
2461-2464
Published: September 25, 1977
Released on J-STAGE: March 31, 2008
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Ein neues Indan-1-ol-Derivat aus den oberirdischen Teilen von Pteris wallichiana AGARDH. wurde als 1 (R), 2 (R), 3 (R)-1, 3-Dihydroxy-2, 5, 7-trimethyl-6-hydroxyathyl-indan-1-O-β-D-glukosid (I) und ein neues Indan-1-on-Derivat aus den oberirdischen Teilen von P. semipinnata L. als 3-Hydroxy-6-hydroxymethyl-2, 5, 7-trimethyl-indan-1-on (XII) identifiziert.
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TERUMI NAKAJIMA, TADASHI YASUHARA
1977 Volume 25 Issue 9 Pages
2464-2465
Published: September 25, 1977
Released on J-STAGE: March 31, 2008
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A new mast cell degranulating peptide was isolated from the frog skin. The peptide possesses a notable sequence, in which hydrophobic amino acid residues are in the N-terminal, and hydrophilic and basic amino acid residues in the C-terminal region. Granuliberin-R belongs to a new family of the active peptides in the amphibian skin.
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NORITO KANEDA, RYOJI KASAI, KAZUO YAMASAKI, OSAMU TANAKA
1977 Volume 25 Issue 9 Pages
2466-2467
Published: September 25, 1977
Released on J-STAGE: March 31, 2008
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By means of enzymatic and chemical procedures, stevioside (1), the major sweet glycoside of Stevia rebaudiana was converted efficiently into another constituent of this plant, rebaudioside-A (2) which tastes sweeter and more pleasant than 1.
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